Domino reaction for the chemo- and stereoselective synthesis of trans-2,3-dihydrobenzofurans from N-thiophosphinyl imines and sulfur ylides

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 7699-7705

  Xie, Peizhong ^a   Wang, Liye ^a   Yang, Lihua ^a   Li, Erqing ^a   Ma, Jianze ^a   Huang, You ^a   Chen, Ruyu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DOMINO REACTIONS; HIGH YIELD; STEREOSELECTIVE SYNTHESIS; SULFUR YLIDES;

NITROGEN COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY; STEREOSELECTIVITY; SULFUR;

SYNTHESIS (CHEMICAL);

DIHYDROBENZOFURAN DERIVATIVE; IMINE; SALICYL N THIOPHOSPHINYL IMINE DERIVATIVE; SULFONIUM DERIVATIVE; TRANS 2,3 DIHYDROBENZOFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DOMINO REACTION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 80054100257     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2008737     Document Type: Article

References (86)

1. (a) Enders, D.; Grondai, C.; Hüttl, M. R. Angew. Chem. Int. Ed. 2007, 46, 1570.
2. (b) Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
3. (c) Guo, H.-C.; Ma, J.-A. Angew. Chem. Int. Ed. 2006, 45, 354.
4. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115.
5. (e) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. 1993, 32, 131.
6. see: (a) Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang. W. J. Am. Chem. Soc. 2007, 129, 1036.
7. (b) Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404.
8. (c) McDougal, N. T.; Schaus, S. E. Angew. Chem. Int. Ed. 2006, 45, 3117.
9. (d) Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem. Int. Ed. 2008, 47, 4177.
10. (e) Yao, W.; Wu, Y.; Wang, G.; Zhang, Y.; Ma, C. Angew. Chem. Int. Ed. 2009, 48, 9713.
11. (f) Filloux, C. M.; Lathrop, S. P.; Rovis, T. Proc. Natl. Acad. Sei. USA. 2010, 107, 20666.
12. (a) Coy, E. D.; Jovanovic, L.; Sefkow, M. Org. Lett. 2010, 12, 1976.
13. (b) Bertolini, F.; Pineschi, M. Org. Prep. Proced. Int. 2009, 41, 385.
14. (c) Sefkow, M. Synthesis 2003, 2595.
15. (a) Meijs, G. F.; Beckwith, A. L. J. J. Am. Chem. Soc. 1986, 108, 5890.
16. (b) Boisvert, G.; Giasson, R Tetrahedron Lett. 1992, 33, 6587.
17. (c) Clive, D. L. J.; Joseph, E.; T., N.; Lown, J. M. J. Org. Chem. 1993, 58, 2442.
18. (d) Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
19. (e) Itoh, T.; Ohara, H.; Emoto, S. Tetrahedron Lett. 1995, 36, 3531.
20. (f) Snider, B. B.; Han, L.; Xie, C. J. Org. Chem. 1997, 62, 6978.
21. (g) Terstiege, L; Maleczka, R E. J. Org. Chem. 1999, 64, 341.
22. (h) Vailard, S. E.; Postigo, A.; Rossi, R. A. J. Org. Chem. 2002, 67, 8500.
23. (i) Kurono, N.; Honda, E.; Komatsu, F.; Orito, K.; Tokuda, M. Tetrahedron 2004, 60, 1791.
24. (j) Lin, H.; Schall, A.; Reiser, O. Synlett 2005, 2603.
25. (k) Park, D. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1440.
26. (a) Barlugenga, J.; Fananas, F. J.; Sanz, R.; Marcis, C. Chem.- Eur. J. 2005, 11, 5397.
27. (b) Kneisel, F. F.; Monguchi, Y.; Knapp, K. M.; Zipse, H.; Knëchel, P. Tetrahedron Lett. 2002, 43, 4875.
28. (c) Plotkin, M.; Chen, S.; Spoors, P. G. Tetrahedron Lett. 2000, 41, 2269.
29. (d) Nakao, J.; Inoue, R.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 1910.
30. (a) Lomberget, T.; Baragona, F.; Fenet, B.; Barret, R Org. Lett. 2006, 8, 3919.
31. (b) Kuethe, J. T.; Wong, A; Journet, M.; Davies, I. W. J. Org. Chem. 2005, 70, 3727.
32. (c) Nair, V.; Rajesh, C.; Dhanya, R; Rath, N. P. Org. Lett. 2002, 4, 953.
33. (d) Apers, S.; Paper, D.; Bürgermeister, J.; Baranikova, S.; Dick, S. V.; Lemière, G.; Vlietinck, A.; Pieters, L. J. Nat. Prod. 2002, 65, 718.
34. (e) Benbow, J. W.; Katoch-Rouse, R J. Org. Chem. 2001, 66, 4965.
35. (f) Engler, T. A; Letavic, M. A; Iyengar, R; LaTessa, K. O.; ReddyJ. P. J. Org. Chem. 1999, 64, 2391.
36. (g) Engler, T. A; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297.
37. (h) Engler, T. A; Combrink, K. D.; Ray, G. E. J. Am. Chem. Soc. 1988, 110, 7931.
38. (a) Kokubo, K.; Harada, K.; Mochizuki, E.; Oshima, T. Tetrahedron Lett. 2010, 51, 955.
39. (b) Engler, T. A; Iyengar, R J. Org. Chem. 1998, 63, 1929.
40. (c) Rupprecht, K. M.; Boger, J.; Koogsteen, K.; Nachbar, R B.; Springer, J. P. J. Org. Chem. 1991, 56, 6180.
41. see: (a) René, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560.
42. (b) Natori, Y.; Tsutsui, H.; Sato, N.; Nakamura, S.; Nambu, H.; Shiro, M.; Hsshimoto, S. J. Org. Chem. 2009, 74, 4418.
43. (c) Szlosek-Pinaud, M.; Diza, P.; Martinez, J.; Lamaty, F. Tetrahedron 2007, 63, 3340.
44. (d) Pelly, S. C.; Govender, S.; Fernandes, M. A; Schmalz, H.-G.; Koning, C. B. J. Org. Chem. 2007, 72, 2857.
45. (e) Grant, V. H.; Liu, B. Tetrahedron Lett. 2005, 46, 1237.
46. (f) Pan, C.; Ma, Z.; Yu, J.; Zhang, Z.; Hui, A; Wang, Z. Synlett 2005, 1922.
47. (g) Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem. Int. Ed. 2004, 43, 6144.
48. (h) Kurosawa, W.; Kobayashi, H.; Kan, T.; Fukuyama, T. Tetrahedron 2004, 60, 9615.
49. (i) Trost, B. M.; Thiel, O. R; Tsui, H.-C. J. Am. Chem. Soc. 2003, 125, 13155.
50. (j) Cheung, W.-H.; Zheng, S.-L.; Yu, W. Y.; Zhou, G.-C; Che, C.-M. Org. Lett. 2003, 5, 2535.
51. (k) Zheng, S. L.; Yu, W. Y.; Xu, M. X.; Che, C.-M. Tetrahedron Lett. 2003, 44, 1445.
52. Kurosawa, W.; Kan, T.; Fukuyama, T. Synlett 2003, 1028.
53. (m) Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
54. (n) Kuwabe, S.-L; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202.
55. (o) Davies, H. M. L.; Grazini, M. V. A; Aouad, E. Org. Lett. 2001, 3, 1475.
56. (a) Shen, Z.; Dong, V. M. Angew. Chem., Int. Ed. 2009, 48, 784.
57. (b) Beltrán-Rodil, S.; Peña, D.; Guitán, E. Synlett 2007, 1308.
58. (c) Liu, G.; Lu, X. J. Am. Chem. Soc. 2006, 128, 16504.
59. see: (a) Lu, X.; Zhang, C.; Xu, Z. ACC. CHEM. RES 2001, 34, 535.
60. (b) Methot, J. L.; Roush, W. R Adv. Synth. Catal. 2004, 346, 1035.
61. (c) Lu, X.; Du, Y.; Lu, C. Pure. Appl. Chem. 2005, 77, 1985.
62. (d) Nair, V.; Menon, R. S.; Sreekanth, A. R; Abhilash, N.; Biji, A T. Acc. Chem. Res. 2006, 39, 520.
63. (e) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
64. (f) Marinetti, A; Voituriez, A. Synlett 2010, 174.
65. (g) Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102.
66. Meng, X.; Huang, Y.; Chen, R. Org. Lett. 2009, 11, 137.
67. Xie, P.; Huang, Y.; Chen, R Org. Lett. 2010, 12, 3768.
68. see: (a) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
69. (b) McGarrigle, E. V.; Myers, E. L.; Illa, O.; Shaw, M. A; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841.
70. (c) Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937.
71. (a) Lu, L.-Q.; Zhang, J.; Li, F.; Cheng, Y.; An, J.; Chen, J.-R.; Xiao, W.-J. Angew. Chem. Int. Ed. 2010, 49, 4495.
72. (b) Lu, L.-Q; Cao, Y.-J.; Liu, X.-P.; Ming, Z.-H.; Xiao, W.-J. J. Am. Chem. Soc. 2008, 130, 6946.
73. (c) Lu, L.-Q.; Li, F.; An, J.; Zhang, J.-J.; An, X.-L.; Hua, Q.-L.; Xiao. W.-I. Angew. Chem., Int. Ed. 2009, 48, 9542.
74. (d) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
75. (e) McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841.
76. (f) Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937.
77. (a) Malik, S.; Nadir, U. P.; Pandey, P. S. Tetrahedron 2009, 65, 3918.
78. (b) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. I. Am. Chem. Soc. 1998, 120, 9690.
79. (c) Zheng, J.-C; Zhu, C.-Y.; Sun, X.-L.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2008, 73, 6909.
80. (d) Zhu, C.-Y.; Deng, X, M.; Sun, X.-L.; Zheng, J.-C; Tang, Y. Chem. Commun. 2008, 738.
81. (e) Zhu, C.-Y.; Sun, X.-L.; Deng, X.-M.; Zheng, J.-C; Tang, Y. Tetrahedron 2004, 64, 5583.
82. (f) Nadir, U. K.; Chaurasia, B. P.; Sharma, R. L. Chem. Lett. 1989, 2023.
83. (a) Meng, X.; Huang, Y.; Chen, R Chem.-Eur. I. 2008, 14, 6852.
84. (b) Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R. Org. Lett. 2009, 11, 991.
85. (c) Ma, J.; Huang, Y.; Chen, R. Org. Biomol. Chem. 2011, 9, 1791.
86. (d) Ma, J.; Xie, P.; Hu, C.; Huang, Y.; Chen, R. Chem.-Eur. J. 2011, 17, 7418.